CN101254475B - 催化剂的再生方法 - Google Patents

催化剂的再生方法 Download PDF

Info

Publication number
CN101254475B
CN101254475B CN2007100510786A CN200710051078A CN101254475B CN 101254475 B CN101254475 B CN 101254475B CN 2007100510786 A CN2007100510786 A CN 2007100510786A CN 200710051078 A CN200710051078 A CN 200710051078A CN 101254475 B CN101254475 B CN 101254475B
Authority
CN
China
Prior art keywords
water
catalyst
acid
phosphine
reaction
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CN2007100510786A
Other languages
English (en)
Chinese (zh)
Other versions
CN101254475A (zh
Inventor
梅尔文·基尔纳
德里克·文森特·泰尔斯
西蒙·彼得·克拉布特里
迈克尔·安东尼·伍德
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Johnson Matthey Davy Technologies Ltd
Original Assignee
DAVID PROCESS TECHNOLOGY Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by DAVID PROCESS TECHNOLOGY Ltd filed Critical DAVID PROCESS TECHNOLOGY Ltd
Publication of CN101254475A publication Critical patent/CN101254475A/zh
Application granted granted Critical
Publication of CN101254475B publication Critical patent/CN101254475B/zh
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/40—Regeneration or reactivation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/40—Regeneration or reactivation
    • B01J31/4015—Regeneration or reactivation of catalysts containing metals
    • B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/40—Regeneration or reactivation
    • B01J31/4015—Regeneration or reactivation of catalysts containing metals
    • B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
    • B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
    • B01J31/4046—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals containing rhodium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/40—Regeneration or reactivation
    • B01J31/4015—Regeneration or reactivation of catalysts containing metals
    • B01J31/4053—Regeneration or reactivation of catalysts containing metals with recovery of phosphorous catalyst system constituents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
    • C07C27/04—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by reduction of oxygen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
    • B01J2531/0258—Flexible ligands, e.g. mainly sp3-carbon framework as exemplified by the "tedicyp" ligand, i.e. cis-cis-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/821—Ruthenium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/822—Rhodium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/824—Palladium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/825—Osmium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/842—Iron
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
    • B01J2531/96—Water
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Furan Compounds (AREA)
  • Pyrane Compounds (AREA)
CN2007100510786A 2002-05-02 2003-04-29 催化剂的再生方法 Expired - Fee Related CN101254475B (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0210143.4 2002-05-02
GBGB0210143.4A GB0210143D0 (en) 2002-05-02 2002-05-02 Process

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CNB038098105A Division CN1314641C (zh) 2002-05-02 2003-04-29 氢化羧酸及其衍生物的均相方法

Publications (2)

Publication Number Publication Date
CN101254475A CN101254475A (zh) 2008-09-03
CN101254475B true CN101254475B (zh) 2012-04-18

Family

ID=9936004

Family Applications (2)

Application Number Title Priority Date Filing Date
CN2007100510786A Expired - Fee Related CN101254475B (zh) 2002-05-02 2003-04-29 催化剂的再生方法
CNB038098105A Expired - Fee Related CN1314641C (zh) 2002-05-02 2003-04-29 氢化羧酸及其衍生物的均相方法

Family Applications After (1)

Application Number Title Priority Date Filing Date
CNB038098105A Expired - Fee Related CN1314641C (zh) 2002-05-02 2003-04-29 氢化羧酸及其衍生物的均相方法

Country Status (19)

Country Link
US (3) US7709689B2 (ko)
EP (2) EP2085141B1 (ko)
JP (2) JP4913342B2 (ko)
KR (2) KR20090031793A (ko)
CN (2) CN101254475B (ko)
AR (1) AR039526A1 (ko)
AU (2) AU2003229955C1 (ko)
BR (1) BR0309585A (ko)
CA (1) CA2483405C (ko)
EA (1) EA009844B1 (ko)
GB (1) GB0210143D0 (ko)
MX (1) MXPA04010699A (ko)
MY (2) MY151328A (ko)
NO (1) NO20045030L (ko)
NZ (1) NZ536088A (ko)
PL (1) PL213001B1 (ko)
TW (1) TWI306412B (ko)
WO (1) WO2003093208A1 (ko)
ZA (1) ZA200408586B (ko)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10173212B2 (en) 2015-04-01 2019-01-08 Hanwha Chemical Corporation Method for regenerating hydrogenation catalyst for phthalate compound

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0325384D0 (en) 2003-10-30 2003-12-03 Davy Process Techn Ltd Process
GB0325526D0 (en) 2003-10-31 2003-12-03 Davy Process Techn Ltd Process
MY144033A (en) 2005-03-08 2011-07-29 Kao Corp Process for producing an alcohol
MX2007012298A (es) 2005-04-05 2007-10-16 Firmenich & Cie Hidrogenacion de esteres con complejos ligandos de ru/tetradentados.
WO2007040087A1 (ja) * 2005-10-03 2007-04-12 Daicel Chemical Industries, Ltd. 酢酸の製造方法
TW200837045A (en) * 2006-09-22 2008-09-16 Lucite Int Uk Ltd Production of amines
EP1970360B1 (en) 2007-03-16 2016-08-31 Takasago International Corporation Method for producing alcohols
JP5283931B2 (ja) * 2007-03-16 2013-09-04 高砂香料工業株式会社 アルコール類の製造方法
ES2537802T3 (es) * 2007-04-03 2015-06-12 Takasago International Corporation Procedimiento de producción de un alcohol mediante hidrogenación de una lactona o un éster de ácido carboxílico en fase líquida
US9290441B2 (en) 2007-10-30 2016-03-22 Yeda Research And Development Co. Ltd. Use of ruthenium complexes for formation and/or hydrogenation of amides and related carboxylic acid derivatives
US7615671B2 (en) * 2007-11-30 2009-11-10 Eastman Chemical Company Hydrogenation process for the preparation of 1,2-diols
US9227896B2 (en) 2010-08-18 2016-01-05 Eastman Chemical Company Process for the separation and purification of a mixed diol stream
US8466328B2 (en) * 2010-08-18 2013-06-18 Eastman Chemical Company Method for recovery and recycle of ruthenium homogeneous catalysts
US8829248B2 (en) 2010-08-18 2014-09-09 Eastman Chemical Company Method for recovery and recycle of ruthenium homogeneous catalysts
US8709376B2 (en) 2010-09-23 2014-04-29 Eastman Chemical Company Process for recovering and recycling an acid catalyst
US8785686B2 (en) 2010-09-23 2014-07-22 Eastman Chemical Company Process for recovering and recycling an acid catalyst
US9045381B2 (en) 2010-10-19 2015-06-02 Yeda Research And Development Co. Ltd. Ruthenium complexes and their uses in processes for formation and/or hydrogenation of esters, amides and derivatives thereof
EP2734299A4 (en) 2011-07-18 2016-05-11 Univ Alberta CATALYSTS AND METHODS FOR HYDROGENATION OF AMIDES
TWI421240B (zh) * 2011-12-12 2014-01-01 Ind Tech Res Inst 苯多羧酸或其衍生物形成環己烷多元酸酯之氫化方法
US8969632B2 (en) 2012-03-23 2015-03-03 Eastman Chemical Company Passivation of a homogeneous hydrogenation catalyst for the production of ethylene glycol
US8703999B2 (en) 2012-03-27 2014-04-22 Eastman Chemical Company Hydrocarboxylation of methylene dipropionate in the presence of propionic acid and a heterogeneous catalyst
US8927766B2 (en) 2012-03-27 2015-01-06 Eastman Chemical Company Hydrocarboxylation of methylene dipropionate in the presence of a propionic acid and a homogeneous catalyst
US8765999B2 (en) 2012-03-27 2014-07-01 Eastman Chemical Company Hydrocarboxylation of formaldehyde in the presence of a higher order carboxylic acid and a homogeneous catalyst
US8829234B2 (en) 2012-03-27 2014-09-09 Eastman Chemical Company Hydrocarboxylation of formaldehyde in the presence of a higher order carboxylic acid and heterogeneous catalyst
US9346737B2 (en) 2013-12-30 2016-05-24 Eastman Chemical Company Processes for making cyclohexane compounds
US9340482B2 (en) 2013-12-30 2016-05-17 Eastman Chemical Company Processes for making cyclohexane compounds
IL234478A0 (en) 2014-09-04 2014-12-02 Yeda Res & Dev Ruthenium complexes and their use for the preparation and/or hydrogenation of esters, amides and their derivatives
IL234479A0 (en) 2014-09-04 2014-12-02 Yeda Res & Dev A liquid hydrogen storage system based on a catalytic process for the preparation and hydrogenation of a cyclic peptide from 2-aminoethanol and 2-(methylamino)ethanol
US9328050B1 (en) 2014-12-23 2016-05-03 Eastman Chemical Company Processes for making hydroxymethylbenzoic acid compounds
JP6551922B2 (ja) * 2015-04-13 2019-07-31 国立大学法人名古屋大学 カルボン酸化合物の水素化によるアルコールの製造方法、及び該製造方法に用いるルテニウム錯体
KR20200082438A (ko) * 2018-12-28 2020-07-08 한화솔루션 주식회사 수소화 촉매의 재생 방법
WO2021109114A1 (en) * 2019-12-06 2021-06-10 Rhodia Operations Supported heterogeneous catalyst, preparation and use thereof
GB202117726D0 (en) 2021-12-08 2022-01-19 Johnson Matthey Plc Process
GB202201979D0 (en) 2022-02-15 2022-03-30 Johnson Matthey Plc Process

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5689003A (en) * 1995-01-31 1997-11-18 E. I. Du Pont De Nemours And Company Ruthenium hydrogenation catalysts

Family Cites Families (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3852346A (en) * 1972-12-26 1974-12-03 Monsanto Co Production of carboxylic acid anhydrides
DE2448005C2 (de) * 1974-10-09 1983-10-20 Basf Ag, 6700 Ludwigshafen Verfahren zur Regenerierung von Rhodium oder Iridium enthaltenden Katalysatoren aus Destillationsrückständen von Hydroformylierungsgemischen
US3957827A (en) * 1974-10-17 1976-05-18 Sun Ventures, Inc. Hydrogenation of carboxylic acid anhydrides to lactones or esters by homogeneous catalysis
US4301077A (en) * 1980-12-22 1981-11-17 Standard Oil Company Process for the manufacture of 1-4-butanediol and tetrahydrofuran
JPS5923858B2 (ja) * 1981-01-22 1984-06-05 三菱化学株式会社 ロジウム錯体の取得方法
US4485245A (en) * 1982-10-29 1984-11-27 Sun Tech, Inc. Hydrogenation of carboxylic acid anhydrides to lactones or esters using a ruthenium trichlorostannate catalyst
US4480115A (en) * 1983-03-17 1984-10-30 Celanese Corporation Direct hydrogenation of carboxylic acids to alcohol and esters
US4892955A (en) 1986-08-19 1990-01-09 Mitsubishi Chemical Industries Limited Method for producing a lactone
JPH07121925B2 (ja) * 1987-04-18 1995-12-25 三菱化学株式会社 ラクトン類の製造法
US4827001A (en) * 1987-11-02 1989-05-02 The Standard Oil Company Preparation of γ-butyrolactone and 1,4-butanediol by catalytic hydrogenation of maleic acid
JPH0272726A (ja) 1988-09-07 1990-03-13 Fujitsu Ltd 伝送路制御方式
JPH089607B2 (ja) 1988-10-31 1996-01-31 三菱化学株式会社 フタライド類の製造法
JPH02200680A (ja) 1989-01-31 1990-08-08 Mitsubishi Kasei Corp γ―ブチロラクトンの製造法
JP2611831B2 (ja) * 1989-01-31 1997-05-21 三菱化学株式会社 １，４―ブタンジオール及び／又はテトラヒドロフランの製造法
JP2516805B2 (ja) 1989-02-06 1996-07-24 三菱化学株式会社 ラクトン類の製造方法
DE3904657A1 (de) * 1989-02-16 1990-08-23 Vdo Schindling Zeigerinstrument
JPH02233674A (ja) 1989-03-07 1990-09-17 Mitsubishi Kasei Corp ラクトン類の製造法
JP2516809B2 (ja) 1989-03-09 1996-07-24 三菱化学株式会社 ラクトン類の製法
JP2516815B2 (ja) 1989-08-11 1996-07-24 三菱化学株式会社 ラクトン類の製造法
JP2785967B2 (ja) 1989-08-25 1998-08-13 三菱化学株式会社 ラクトン類の製造方法
JPH07121928B2 (ja) 1989-10-24 1995-12-25 三菱化学株式会社 ラクトン類の精製法
JPH07121929B2 (ja) * 1990-08-03 1995-12-25 三菱化学株式会社 ラクトン類の製造法
JP2825286B2 (ja) 1989-09-27 1998-11-18 三菱化学株式会社 ラクトン類の製造法
US5047561A (en) 1989-09-27 1991-09-10 Mitsubishi Kasei Corporation Process for producing a lactone
JP2516836B2 (ja) * 1989-10-04 1996-07-24 三菱化学株式会社 ラクトン類の製造法
US5077442A (en) * 1990-04-26 1991-12-31 Mitsubishi Kasei Corporation Method for producing 1,4-butanediol
JP2796884B2 (ja) * 1990-08-30 1998-09-10 高砂香料工業株式会社 光学活性γ―ブチロラクトン誘導体の製造方法
JP2906706B2 (ja) 1990-10-08 1999-06-21 三菱化学株式会社 １，４−ブタンジオールの製造法
US5107053A (en) * 1990-12-10 1992-04-21 Ethyl Corporation Ruthenium phosphine complex
US5118825A (en) * 1990-12-10 1992-06-02 Ethyl Corporation Ruthenium phosphine complex
JPH06107654A (ja) 1992-09-29 1994-04-19 Tosoh Corp ラクトン類の製造法
JP3194803B2 (ja) 1992-12-03 2001-08-06 東ソー株式会社 ラクトン類の製造方法
JPH0733756A (ja) 1993-06-28 1995-02-03 Tosoh Corp ラクトン類を製造する方法
JPH0782260A (ja) 1993-09-14 1995-03-28 Tosoh Corp ラクトン類の製法
TW319771B (ko) 1994-04-05 1997-11-11 Mitsubishi Chem Corp
JP3756543B2 (ja) * 1994-04-05 2006-03-15 三菱化学株式会社 有機リン−ルテニウム錯体触媒成分の分離および再使用方法
US5599962A (en) * 1995-01-31 1997-02-04 E. I. Du Pont De Nemours And Company Process for the preparation of ruthenium hydrogenation catalysts and products thereof
JP3204870B2 (ja) 1995-04-11 2001-09-04 株式会社日本製鋼所 中空成形機のエアー吹込方法及びその装置
JP3083974B2 (ja) 1995-04-15 2000-09-04 新日本製鐵株式会社 巻回コイル吊下治具
JP3141273B2 (ja) 1995-07-24 2001-03-05 株式会社ジャンボトクラ 臀部を露出可能な衣服
US5599262A (en) * 1995-12-21 1997-02-04 Shih; Ching-Fu Shake and twist exerciser
JP3074377B2 (ja) 1997-03-06 2000-08-07 セイコーインスツルメンツ株式会社 端面研磨装置および研磨方法
DE19720657A1 (de) 1997-05-16 1998-11-19 Basf Ag Verfahren zur Herstellung von aliphatischen Alkoholen
US6133477A (en) * 1997-07-23 2000-10-17 E. I. Du Pont De Nemours And Company Preparation of 3-pentenoic acid
US6008384A (en) * 1998-03-03 1999-12-28 E. I. Du Pont De Nemours And Company Method and Ru,Re,Sn/carbon catalyst for hydrogenation in aqueous solution
JP2000034244A (ja) * 1998-07-16 2000-02-02 Mitsubishi Chemicals Corp １，４−ブタンジオール及び／又はテトラヒドロフランの製造方法
US6084526A (en) 1999-05-12 2000-07-04 Time Warner Entertainment Co., L.P. Container with means for displaying still and moving images
DE69934109D1 (de) 1999-08-18 2007-01-04 Ineos Usa Llc Verbesserte Katalysatoren zur Hydrierung von Maleinsäure zu 1,4-Butandiol
JP4217636B2 (ja) 2003-02-28 2009-02-04 文化シヤッター株式会社 開閉装置
JP3112973U (ja) 2005-04-15 2005-09-02 陽之 大瀬 開脚角度を自由に変えられる二重補助支脚式簡易スタンド
JP4091085B2 (ja) 2006-04-05 2008-05-28 株式会社日立国際電気 画像記録装置及び画像記録方法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5689003A (en) * 1995-01-31 1997-11-18 E. I. Du Pont De Nemours And Company Ruthenium hydrogenation catalysts

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10173212B2 (en) 2015-04-01 2019-01-08 Hanwha Chemical Corporation Method for regenerating hydrogenation catalyst for phthalate compound

Also Published As

Publication number Publication date
EA200401461A1 (ru) 2005-04-28
KR20040111567A (ko) 2004-12-31
US7709689B2 (en) 2010-05-04
EP2085141A1 (en) 2009-08-05
JP5230561B2 (ja) 2013-07-10
MXPA04010699A (es) 2005-02-17
EP2085141B1 (en) 2016-12-07
NZ536088A (en) 2006-05-26
JP4913342B2 (ja) 2012-04-11
KR20090031793A (ko) 2009-03-27
NO20045030L (no) 2004-11-19
PL213001B1 (pl) 2012-12-31
AU2003229955B2 (en) 2009-11-26
US20050234269A1 (en) 2005-10-20
CA2483405A1 (en) 2003-11-13
EP1499573A1 (en) 2005-01-26
GB0210143D0 (en) 2002-06-12
MY151328A (en) 2014-05-15
PL373292A1 (en) 2005-08-22
EP1499573B1 (en) 2013-07-24
CA2483405C (en) 2012-10-02
AU2003229955C1 (en) 2013-10-31
JP2005524704A (ja) 2005-08-18
CN101254475A (zh) 2008-09-03
AU2009233665B2 (en) 2011-05-19
MY149091A (en) 2013-07-15
US20130029831A1 (en) 2013-01-31
WO2003093208A1 (en) 2003-11-13
ZA200408586B (en) 2006-10-25
AR039526A1 (es) 2005-02-23
JP2009269031A (ja) 2009-11-19
TWI306412B (en) 2009-02-21
CN1314641C (zh) 2007-05-09
TW200402327A (en) 2004-02-16
BR0309585A (pt) 2005-03-01
AU2009233665A1 (en) 2009-11-26
AU2003229955A1 (en) 2003-11-17
EA009844B1 (ru) 2008-04-28
US9636671B2 (en) 2017-05-02
US20100099550A1 (en) 2010-04-22
CN1649809A (zh) 2005-08-03

Similar Documents

Publication Publication Date Title
CN101254475B (zh) 催化剂的再生方法
CN101124191A (zh) 生产醋酸的方法
CN104080760A (zh) 由烯烃制备醇的装置和方法
CN101367698A (zh) 用来由乙烷制备乙烯和一氧化碳混合物的方法
AU615985B2 (en) Thee production of formic acid from a nitrogenous base, carbon dioxide and hydrogen
CN100467433C (zh) 二羧酸和/或其酐的均相氢化方法
Fang et al. Domino hydroformylation/aldol condensation/hydrogenation catalysis: highly selective synthesis of ketones from olefins
Zhang et al. The preparation and catalytic performance of novel amine-modified silica supported ruthenium complexes for supercritical carbon dioxide hydrogenation to formic acid
CN103764284B (zh) 官能化的烯烃的烷氧基羰基化方法
CN103619801A (zh) 使用钯二齿二磷酸配体在羰基化方法中制备烷酸酯的方法
Wegman et al. The role of phosphines and solvents in CoI2-catalyzed reductive carbonylation of methanol
Kostera et al. Manganese (I) Catalyzed CO2 Reduction Processes in Homogenous Phase
US6294687B1 (en) Process for the preparation of saturated carboxylic acids and their esters
JPH03163040A (ja) ヒドロホルミル化法
Li Studies in hydrocarboxylation of styrene and derivatives using palladium complex catalysts
KR20040050998A (ko) 초임계 이산화탄소를 반응 용매로 하는 에스테르 유도체의선택적 제조 방법
JPH01203346A (ja) ２−クロロプロピオンアルデヒドの製造法

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CP01 Change in the name or title of a patent holder

Address after: London, England

Patentee after: JOHNSON MATTHEY DAVY TECHNOLOGIES LTD.

Address before: London, England

Patentee before: DAVY PROCESS TECHNOLOGY LTD.

CP01 Change in the name or title of a patent holder
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20120418

CF01 Termination of patent right due to non-payment of annual fee